Triethylamine → HCID 9848186, compound

HRID 1456371Notes

Reaction equation

HRID 1456371 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)=[C:4](C(O)=O)[C:3]1=[O:23].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.C([N:43]([CH2:46]C)CC)C.[CH:48]([C:51]1[CH:57]=[CH:56][CH:55]=[C:54]([CH:58]([CH3:60])[CH3:59])[C:52]=1[NH2:53])([CH3:50])[CH3:49]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)=[C:4]([NH:43][C:46]([NH:53][C:52]2[C:51]([CH:48]([CH3:50])[CH3:49])=[CH:57][CH:56]=[CH:55][C:54]=2[CH:58]([CH3:60])[CH3:59])=[O:31])[C:3]1=[O:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 32484DiisopropylanilineHCID 199401P,P-Diphenylphosphinic azideHCID 22106065HCID 22106065, compound

Product 1

HCID 9848186HCID 9848186, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-methyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine-3-carboxylic acid (315 mg, 1 mmol), diphenylphosphoryl azide (330 mg, 1.2 mmol) and triethylamine (101 mg, 1 mmol) in toluene (4 ml) was stirred at room temperature for 0.5 hour, and then refluxed for 0.5 hour. After allowed to stand for cooling, to the mixture was added 2,6-diisopropylaniline (216 mg, 1.2 mmol), and the mixture was stirred at room temperature for 0.5 hour, and then stirred under reflux for two hours. After allowed to stand for cooling, the mixture was diluted with ethyl acetate, washed with water, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The resultant was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane =1:1), and crystallized from diethyl ether to give the title compound (302 mg, 0.62 mmol) as a colorless crystal.

Workup

  1. temperaturerefluxed for 0.5 hour
  2. temperaturefor cooling, to the mixture
  3. stirringstirred
  4. temperatureunder reflux for two hours
  5. temperaturefor cooling
  6. washwashed with water
  7. washwashed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationThe resultant was concentrated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane =1:1)
  11. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-d1e95699ccff4241912f0618791f888f
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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